Eastern Massachusetts Beach Vacations

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Top Beach vacation packages in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
The Mansion at Ocean Edge

The Mansion at Ocean Edge

$1,248
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Boston (BOS)
8.2/10 Very Good! (1,006 reviews)
I enjoyed the spacious room and private balcony. The indoor hot tub and pool were very clean. The food was excellent and the staff was wonderful

Reviewed on Oct 8, 2026

Harbor View Hotel

Harbor View Hotel

$1,597
per person
Dec 18 - Dec 22
found 2 hours ago
Roundtrip flight included
Lexington (LEX) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
This is a hard hotel to review. We felt that there was a bit of an issue with the staff as it all seemed a bit joyless and there were trays of room service food just left in the corridors for ages. And at the checkout having spent a lot of money on 2 nights in one of the best rooms they sought to charge us an extra $54.29 per day for a ""resort fee" which apparently included using the pool and general amenities!! We queried this and it was then taken off the bill. On the other hand the hotel was very generous and gave us some lovely chocolate fresh strawberries and wine for our anniversary and breakfast on one occasion. The staff were very nice but there seemed to be a lack of an obvious manager - ie no one to conduct the orchestra. So a mixed bag! We stayed in the old building looking out at the most amazing view and the bed could not have been more comfortable. But below us the room had the TV on very loud all afternoon and night and there is little sound insulation so that was pretty annoying! It is a really beautiful hotel in an extraordinary location with a great (and very expensive!) restaurant!

Reviewed on Oct 9, 2026

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5* Beach vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
Harbor View Hotel

Harbor View Hotel

$1,597
per person
Dec 18 - Dec 22
found 2 hours ago
Roundtrip flight included
Lexington (LEX) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
This is a hard hotel to review. We felt that there was a bit of an issue with the staff as it all seemed a bit joyless and there were trays of room service food just left in the corridors for ages. And at the checkout having spent a lot of money on 2 nights in one of the best rooms they sought to charge us an extra $54.29 per day for a ""resort fee" which apparently included using the pool and general amenities!! We queried this and it was then taken off the bill. On the other hand the hotel was very generous and gave us some lovely chocolate fresh strawberries and wine for our anniversary and breakfast on one occasion. The staff were very nice but there seemed to be a lack of an obvious manager - ie no one to conduct the orchestra. So a mixed bag! We stayed in the old building looking out at the most amazing view and the bed could not have been more comfortable. But below us the room had the TV on very loud all afternoon and night and there is little sound insulation so that was pretty annoying! It is a really beautiful hotel in an extraordinary location with a great (and very expensive!) restaurant!

Reviewed on Oct 9, 2026

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3 Night Beach vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
The Mansion at Ocean Edge

The Mansion at Ocean Edge

$754
per person
Nov 25 - Nov 28
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Boston (BOS)
8.2/10 Very Good! (1,006 reviews)
I enjoyed the spacious room and private balcony. The indoor hot tub and pool were very clean. The food was excellent and the staff was wonderful

Reviewed on Oct 8, 2026

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4 Night Beach vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.
The Mansion at Ocean Edge

The Mansion at Ocean Edge

$645
per person
Nov 17 - Nov 21
found 9 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Boston (BOS)
8.2/10 Very Good! (1,006 reviews)
I enjoyed the spacious room and private balcony. The indoor hot tub and pool were very clean. The food was excellent and the staff was wonderful

Reviewed on Oct 8, 2026

Harbor Hotel Provincetown

Harbor Hotel Provincetown

Save 100% on your flight
$14,840
per person
Dec 20 - Dec 24
found 8 hours ago
Roundtrip flight included
Orlando (MCO) to Provincetown (PVC)
8.4/10 Very Good! (1,005 reviews)
Issue with hot water; took over 5 minutes to become warm; nowhere to put clothes other than a top shelf in the one open closet. Beds were very comfortable. Staff very friendly

Reviewed on Oct 7, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

$687
per person
Nov 12 - Nov 16
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (245 reviews)
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Find your perfect Eastern Massachusetts beach vacation

How do I book the best Eastern Massachusetts beach vacation packages?

Life’s a beach when you dive into our brilliant Eastern Massachusetts beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Eastern Massachusetts?

A rental steps from the shore creates an amazingly affordable Eastern Massachusetts beach vacation. Seaside sojourns during low season start from $645. Prices and availability are subject to change. Additional terms may apply.

When should I book a Eastern Massachusetts beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Eastern Massachusetts?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Eastern Massachusetts beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Eastern Massachusetts vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Eastern Massachusetts beach vacation deals?

Sort your search results by deals to delight in amazing Eastern Massachusetts beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Eastern Massachusetts beach trip with free cancellation and/or flexible dates?

Just like the Eastern Massachusetts tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Eastern Massachusetts beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Eastern Massachusetts. (OK, maybe not that last part.)

Top Beach Eastern Massachusetts Hotels

The Westin Boston Seaport District

The Westin Boston Seaport District

425 Summer St Boston MA
  • 5 min walk from Fenway Park
At this hotel, get ready to lounge by the shoreline in Boston, as you'll be near the beach. 2 bars, an indoor pool, and a restaurant are just some of the amenities ...
9.2/10 Wonderful! (2,437 reviews)

Travelers like: close to beach, indoor pool

Travelers say...
"Beautiful property and everyone was welcoming, courteous and professional from the time we walked in to helping arrange a car to the airport the next morning. Will definitely stay here again when in the Boston area."

Reviewed on Oct 8, 2026

The Westin Boston Seaport District
Sea Crest Beach Resort

Sea Crest Beach Resort

350 Quaker Rd North Falmouth MA
  • 2 hours drive from Fenway Park
At this hotel, get ready to enjoy the sunsets on the beach in North Falmouth, as you'll be near Cape Cod Beaches. 2 restaurants, a private beach, and a beach ...
7.6/10 Good! (529 reviews)

Travelers like: on the beach, sun loungers, beach bars, beach umbrellas

Travelers say...
"No microwave and the bathroom needs upgraded. Better locks on outside doors."

Reviewed on Oct 8, 2026

Sea Crest Beach Resort
Lighthouse Inn

Lighthouse Inn

1 Lighthouse Inn Rd West Dennis MA
  • 2 hours drive from Fenway Park
Make the most of this fantastic location, as you'll be a short walk from Cape Cod Beaches with a holiday at this hotel. Amenities at Lighthouse Inn include a ...
8.8/10 Excellent! (335 reviews)

Travelers like: on the beach, sun loungers, beach umbrellas, beach towels

Travelers say...
"The food in the restaurant was amazing and the staff were helpful. The hotel is in a nice area, and was great for exploring cape cod. The room was very small and lacked any modern amenities and was quite damp and not very pleasant. It was ok as a place to sleep but nothing more than that."

Reviewed on Oct 8, 2026

Lighthouse Inn
See all 16,071 properties in Eastern Massachusetts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Things to do

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)

$50
per adult
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

$17
per traveler
80% of travellers recommend
Cape Ann Self-Guided Driving Tour in Gloucester and Rockport
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Eastern Massachusetts

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.